Cesium carbonate → N-(3-(5-chloro-2-((3-fluoro-4-morpholinophenyl)amino)pyrimidin-4-yl)phenyl)acrylamide

Participants

Reaction Conditions

Reaction Steps

N-(3-(2,5-dichloropyrimidin-4-yl)phenyl)acrylamide (50 mg, 0.170 mmol), 3-fluoro-4-morpholinoaniline (33.4 mg, 0.170 mmol) and Cs2CO3 (66.5 mg, 0.204 mmol) were dissolved in toluene (5 ml) in a sealable microwave compatible reaction tube, then Pd2(dba)3 (3.11 mg, 3.40 μmol) and X-phos (3.93 mg, 6.80 μmol) were added. The reaction tube was sealed and the reaction was heated under microwave irradiation (60 min, 200° C., 3 atm). The reaction was monitored by TLC and after completion of the reaction, the solvent was in vacuo. The compound was purified by column chromatography (10% CH3OH/CH2Cl2) to yield N-(3-(5-chloro-2-((3-fluoro-4-morpholinophenyl)amino)pyrimidin-4-yl)phenyl)acrylamide (26 mg, 0.056 mmol, 32.7% yield) as a solid. 1H NMR (400 MHz, CD3OD): δ 8.43 (s, 1H), 8.22 (s, 1H), 7.75 (d, 1H, J=7.2 Hz), 7.65-7.57 (m, 2H), 7.45 (t, 1H, J=8.0 Hz), 7.34 (m, 1H), 6.94 (t, 1H, J=9.2 Hz), 6.40 (m, 2H), 5.78 (dd, 1H, J=2.0 & 9.6 Hz), 3.80 (m, 4H), 2.98 (m, 4H). ESI-MS: m/z 454.1 [M+H]+.

Provenance & Evidence